Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → 3-[4-(2-t-Butylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid ethyl ester

HRID 62930Notes

Reaction equation

HRID 62930 reaction equation
[C:1]([S:5][C:6]1[C:11]([CH2:12]Cl)=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:16][C:17](=[O:29])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([OH:27])=[C:22]([F:28])[CH:21]=1)[CH3:15]>>[CH2:14]([O:16][C:17](=[O:29])[CH2:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([O:27][CH2:12][C:11]2[C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:7][CH:8]=[CH:9][CH:10]=2)=[C:22]([F:28])[CH:21]=1)[CH3:15]

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 901182022-t-Butylsulfanyl-3-chloromethyl-pyridine

Product 1

HCID 901186713-[4-(2-t-Butylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid ethyl esterYield 86%

Procedure

2-t-Butylsulfanyl-3-chloromethyl-pyridine (0.08 g, 0.37 mmol) obtained in Step C of Preparation Example 17 and 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester obtained in Step D of Preparation Example 2 were used to react in the same manner as in Step A of Example 1 to obtain the title compound (0.13 g, 86%).

Workup

  1. customto react in the same manner as in Step A of Example 1

Sources & evidence

ORD record
ord-867258840b3d4f1691395980e6e92a31
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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